Bioactive long chain N-acylethanolamines in five species of edible bivalve molluscs. Possible implications for mollusc physiology and sea food industry.
Several long chain N-acylethanolamines, including the proposed endogenous ligands of cannabinoid receptors, anandamide (N-arachidonoylethanolamine, C20:4 NAE) and N-palmitoylethanolamine (C16:0 NAE), as well as some of their putative biosynthetic precursors, the N-acyl-phosphatidylethanolamines, were found in lipid extracts of five species of bivalve molluscs, including Mytilus galloprovincialis, commonly used as sea food. The amounts of these metabolites, the most abundant being C16:0 NAE and N-stearoylethanolamine, appeared to increase considerably when mussels were extracted 24h post-mortem, but were not significantly affected by boiling the tissue prior to extraction. In particulate fractions of homogenates from Mytilus, where the existence of a highly selective cannabinoid receptor with an immunomodulatory function has been previously described, an enzymatic activity capable of catalyzing the hydrolysis of C20:4 NAE amide bond, and displaying similar pH dependency and inhibitor sensitivity profiles as the recently characterized 'fatty acid amide hydrolase' was found. The enzyme Km and Vmax for C20:4 NAE were 29.6 microM and 73 pmol/mg protein/min, respectively. These findings support the hypothesis that C20:4 NAE, never reported before in the phylum Mollusca, may be a mollusc physiological mediator, and suggest that edible bivalves may be a dietary, albeit limited, source of C16:0 NAE, whose anti-inflammatory properties, when administered orally in amounts higher than those reported here, have been previously reported.
Sepe
N
N
Istituto per la Chimica di Molecole di Interesse Biologico, C.N.R., Arco Felice (Na), Italy.
De Petrocellis
L
L
Montanaro
F
F
Cimino
G
G
Di Marzo
V
V
D000577:Amides; D000581:Amidohydrolases / Q000032:analysis / Q000378:metabolism; D000818:Animals; D063388:Endocannabinoids; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004983:Ethanolamines / Q000032:analysis* / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D007700:Kinetics; D008024:Ligands; D008974:Mollusca / Q000737:chemistry* / Q000502:physiology; D010169:Palmitic Acids / Q000032:analysis; D010714:Phosphatidylethanolamines / Q000032:analysis; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000819:agonists; D000099252:Fatty Acid Amide Hydrolases
D000577:Amides; D000581:Amidohydrolases; D063388:Endocannabinoids; D004791:Enzyme Inhibitors; D004983:Ethanolamines; D008024:Ligands; D010169:Palmitic Acids; D010714:Phosphatidylethanolamines; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; D000099252:Fatty Acid Amide Hydrolases; C022203:N-acylethanolamines; C109143:N-arachidonylphosphatidylethanolamine; C005958:palmidrol